Benzyl Chloride → 1-(Benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylic acid

HRID 1041834Notes

Reaction equation

HRID 1041834 reaction equation
[OH:1][N:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]1=[O:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[CH2:18]([O:1][N:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]1=[O:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 110841061-Hydroxy-6-oxo-1,6-dihydropyridine-2-carboxylic acid

Product 1

HCID 154505551-(Benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Hydroxy-6-carboxy-2 (1H)-pyridinone (15.5 g, 0.1 mol) and anhydrous potassium carbonate (27.6 g, 0.2 mol) were mixed with benzyl chloride (15.2 g, 0.12 mol) in methanol (250 mL). The mixture was refluxed for 16 h, filtered, and the filtrate evaporated to dryness. The residue was dissolved in water (50 mL) and acidified with 6 N HCl to pH 2. The white precipitate was isolated by filtration, washed with cold water, and dried in vacuum, to yield 22.3 g (91%) of 1-Benzyloxy-6-carboxy-2 (1H)-pyridinone, mp 176-177° C.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. dissolutionThe residue was dissolved in water (50 mL)
  5. customThe white precipitate was isolated by filtration
  6. washwashed with cold water
  7. customdried in vacuum

Sources & evidence

ORD record
ord-df182a05190b45f0a62d5533404fe5cf
Source dataset
uspto-grants-2013_10
Patent number
US08557601B2

Reaction notes

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